Oxazolidinone derivatives, processes for the production thereof and pharmaceutical agents containing these compounds

Abstract

The present invention concerns new oxazolidinone derivatives, processes for their production as well as pharmaceutical agents containing these substances. The present invention concerns compounds of the general formula I in which the symbols have the meanings as listed in the claims.

We claim: 
     
       1. A compound of formula I, ##STR16## wherein X, Y and Q are independently selected from the group consisting of nitrogen and CH; W is selected from the group consisting of hydrogen and --NR 0  R 00  ;   Z is selected from the group consisting of nitrogen, CH and C--OH;   A, E, and G are independently selected from the group consisting of a valency bond and an alkylene chain --(CH 2 ) n-  ;   B is a valency bond or when Z is nitrogen, B is a carbonyl group;   D is a side chain of the formula --(CHR 3 ) m  --COO-- or ═CR 3  --COO--;   n is 1-5;   m is 0 or 1;   R 1  and R 2  are independently selected from the group consisting of hydrogen, C 1-6  alkyl, and aryl or R 1  and R 2  together form a carbocyclic five-membered or six-membered ring,   R 3  is selected from the group consisting of hydrogen, --OR 5  and --NR 6  R 7  ;   R 4  is selected from the group consisting of hydrogen and --OR 5  ;   R 5  is selected from the group consisting of hydrogen, C 1-6  alkyl, aryl and arylC 1-6  alkyl;   R 6  is selected from the group consisting of hydrogen, C 1-6  alkyl and arylC 1-6  alkyl;   R 7  is selected from the group consisting of hydrogen, C 1-6  alkyl, arylC 1-6  alkyl, acyl, C 1-4  alkylsulfonyl and arylsulfonyl;   R 0  and R 00  are independently selected from the group consisting of hydrogen, C 1-6  alkyl, aryl, arylC 1-6  alkyl, hetaryl, acyl and a carbocyclic or heterocyclic ring which is unsubstituted or substituted at least once with a C 1-6  alkyl, or R 0  and R 00  together with the nitrogen to which they are bound form a five-membered or six-membered ring which is unsubstituted or substituted at least once with a C 1-6  alkyl, as well as conformational isomers and pharmacologically acceptable salts thereof.     
     
     
       2. The compound according to claim 1, wherein R 0  and R 00  together with the nitrogen to which they are bound form a five-membered or six-membered ring which is unsubstituted or substituted at least once with a C 1-6  alkyl and contains 1-3 additional heteroatoms. 
     
     
       3. The compound according to claim 1, wherein n is selected from the group consisting of 1, 2 and 3. 
     
     
       4. The compound according to claim 1, wherein each aryl is a phenyl residue. 
     
     
       5. The compound according to claim 1, wherein each acyl is independently selected from the group consisting of formyl, acetyl, propionyl, butyryl and benzoyl residues. 
     
     
       6. The compound according to claim 1, wherein arylsulfonyl is selected from the group consisting of benzene sulfonic acid and toluene sulfonic acid. 
     
     
       7. A compound according to claim 1, wherein said compound is selected from the group consisting of 1-[(5S)-2-oxo-3-(3,4,5,6-tetrahydro-2H-[1, 4']bipyridinyl-4-yl)-oxazolidin-5-ylmethyl]piperidine-4-carboxylic acid 1-[(rac)-2-oxo-3-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-oxazolidin-5-ylmethyl]-piperidine-4-carboxylic acid   {1-[(rac)-2-oxo-3-(3,4,5,6-tetrahydro-2H-[1, 4']bipyridinyl 4-yl)-oxazolidin-5-ylmethyl]-piperidin-4-ylidene}-acetic acid   {4-hydroxy-1-[2-oxo-3-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-oxazolidin-5-ylmethyl]-piperidin-4-yl}-acetic acid   1-[4-methyl-2-oxo-3-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-oxazolidin-5-ylmethyl]-piperidine-4-carboxylic acid   1-[2-oxo-4-phenyl-3-(3,4,5,6-tetrahydro-2H-[1, 4']bipyridinyl-4-yl)-oxazolidin-5-ylmethyl]-piperidine-4-carboxylic acid   1-[2-oxo-3-(1-pyrimidine-4-yl-piperidine-4-yl) oxazolidin-5-ylmethyl]-piperidine-4-carboxylic acid   1-{3-[1-(2-benzylamino-pyrimidine-4-yl)-piperidine-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-piperidin-4-carboxylic acid   4-hydroxy-4-[2-oxo-3-(3,4,5,6-tetrahydro-2H-[1, 4']bipyridinyl 4-yl)-oxazolidin-5-ylmethyl]-cyclohexanecarboxylic acid   (5S)-1-[5-methyl-2-oxo-3-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl) -oxazolidin-5-ylmethyl]-piperidine-4-carboxylic acid   1-[2-oxo-3-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)-4-(3-trifluoromethylphenyl)-oxazolidin-5-ylmethyl]-piperidine-4-carboxylic acid, and   1-[4-(4-chloro-phenyl)-2-oxo-3-(3,4,5,6-tetrahydro-2H -[1,4']bipyridinyl-4-yl)-oxazolidin-5-ylmethyl]-piperidine-4-carboxylic acid and the conformational isomers and pharmacologically acceptable salts thereof.       
     
     
       8. A pharmaceutical composition for inhibiting the aggregation of blood platelets, comprising an aggregation inhibiting amount of at least one compound according to claim 6 in combination with a pharmaceutically acceptable carrier. 
     
     
       9. A method for inhibiting blood platelet aggregation, comprising administering an amount of a compound according to claim 1 effective to inhibit blood platelet aggregation to a patient in need of such treatment. 
     
     
       10. A method for treating a condition caused by a thromboembolic occurrence resulting from blood platelet aggregation, comprising administering an amount of a compound according to claim 1 effective to inhibit blood platelet aggregation to a patient in need of such treatment. 
     
     
       11. The method according to claim 10, wherein said condition caused by a thromboembolic occurrence is selected from the group consisting of stroke, myocardial infarction and arterial occlusion.